Triethylamine → Ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate

HRID 714931Notes

Reaction equation

[C:1]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[BrH:24].[NH+]1C=CC=CC=1.CCOC(C)=O>C(O)C>[Br:24][CH:11]([C:1]([C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)=[O:10])[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl p-anisoylacetate (1.00 g, 4.5 mmol) in ethanol (14 mL) at 50° C. was added triethylamine (0.63 mL, 4.5 mmol) followed by pyridinium hydrobromide perbromide (1.44 g, 4.5 mmol) and the resulting mixture was then stirred at 50° C. for 2 hours. The reaction was cooled to room temperature and poured into EtOAc. The organic phase was then washed with saturated sodium bicarbonate solution and 0.5M aqueous HCl, dried over MgSO4 and the solvent removed in vacuo to afford ethyl 2-bromo-3-(4-methoxyphenyl)-3-oxopropanoate (1.209 g, 4.0 mmol, 89%) which was used without further purification. 1H NMR (CDCl3) δ 1.26 (3H, t), 3.89 (3H, s), 4.28 (2H, q), 5.62 (1H, s), 6.96 (2H, d), 7.98 (2H, d). LCMS (2) Rt: 3.06 min; m/z (ES+) 301/303.

Workup

temperatureThe reaction was cooled to room temperature
washThe organic phase was then washed with saturated sodium bicarbonate solution and 0.5M aqueous HCl
dry with materialdried over MgSO4
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-b055093532a44040bed4c968f6ef12d4
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187465B2

Reaction notes

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